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Apartments in Province of Siena and Villas – Holiday Lettings - Holiday Rentals Province of Siena

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4,570 Holiday homes

B&b rental in Chiusure with shared pool

Chiusure b&b

6 bedrooms • 6 bathrooms • sleeps 14

from £115 / night

£885 / week

Holiday villa with swimming pool in Montisi

Montisi villa

3 bedrooms • 3 bathrooms • sleeps 8

from £23 / night

£162 - £2,388 / week

Apartment rental in Siena

Siena apartment

1 bedroom • 1 bathroom • sleeps 4

23 Reviews

from £114 / night

£1,157 / week

Farmhouse rental in Radicofani with shared pool

Radicofani farmhouse

2 bedrooms • 2 bathrooms • sleeps 4

4 Reviews

from £119 / night

£829 / week

Apartment rental in Radicondoli with shared pool

Radicondoli apartment

1 bedroom • 1 bathroom • sleeps 2

from £113 / night

£791 / week

Holiday apartment with shared pool in Gaiole in Chianti

Gaiole in Chianti apartment

2 bedrooms • 2 bathrooms • sleeps 6

7 Reviews

from £106 / night

£740 - £1,081 / week

Holiday farmhouse in Castelnuovo Berardenga

Castelnuovo Berardenga farmhouse

2 bedrooms • 2 bathrooms • sleeps 4

11 Reviews

from £93 / night

£648 / week

Holiday guest house in Radicondoli

Radicondoli guest house

3 bedrooms • 4 bathrooms • sleeps 5

2 Reviews

from £160 / night

£697 / week

Holiday townhouse with swimming pool in Sovicille

Sovicille townhouse

2 bedrooms • 2 bathrooms • sleeps 5

18 Reviews

from £113 / night

£788 / week

Holiday apartment rental

Montepulciano apartment

2 bedrooms • 1 bathroom • sleeps 7

1 Reviews

from £64 / night

£427 - £792 / week

San Gimignano holiday b&b accommodation

San Gimignano b&b

1 bedroom • 1 bathroom • sleeps 2

from £57 / night

£395 / week

Montepulciano holiday b&b rental

Montepulciano b&b

6 bedrooms • 5 bathrooms • sleeps 12

3 Reviews

from £313 / night

£2,187 / week

San Gimignano holiday villa accommodation

San Gimignano villa

3 bedrooms • 2 bathrooms • sleeps 6

23 Reviews

from £107 / night

£746 / week

Cottage rental in Pancole

Pancole cottage

1 bedroom • 1 bathroom • sleeps 3

34 Reviews

from £50 / night

£331 - £513 / week

Radicofani holiday apartment rental

Radicofani apartment

1 bedroom • 1 bathroom • sleeps 4

from £88 / night

£616 / week

Holiday home rental

Montepulciano house

4 bedrooms • 4 bathrooms • sleeps 8

2 Reviews

from £360 / night

£2,514 / week

Holiday villa rental

Colle di Val d'Elsa villa

2 bedrooms • 3 bathrooms • sleeps 6

from £158 / night

£2,570 / week

Sarteano holiday townhouse rental

Sarteano townhouse

1 bedroom • 1 bathroom • sleeps 2

2 Reviews

from £79 / night

£553 / week

Castelnuovo dell'Abate holiday apartment rental

Castelnuovo dell'Abate apartment

1 bedroom • 1 bathroom • sleeps 4

6 Reviews

from £93 / night

£647 / week

Holiday home in Radicondoli

Radicondoli house

3 bedrooms • 2 bathrooms • sleeps 6

from £242 / night

£1,693 / week

Holiday villa with shared pool in Val d'Orcia

Val d'Orcia villa

2 bedrooms • 2 bathrooms • sleeps 6

1 Reviews

from £112 / night

£618 - £1,438 / week

Holiday apartment in Monticiano

Monticiano apartment

2 bedrooms • 1 bathroom • sleeps 4

2 Reviews

from £62 / night

£411 / week

Holiday farmhouse rental

Montepulciano farmhouse

9 bedrooms • 9 bathrooms • sleeps 18

from £820 / night

£4,203 / week

Holiday apartment rental

Cetona apartment

1 bedroom • 1 bathroom • sleeps 3

6 Reviews

from £58 / night

£401 - £521 / week

Ski apartment to rent in Pienza

Pienza apartment

1 bedroom • 1 bathroom • sleeps 2

from £72 / night

£411 / week

Holiday villa rental

Torri villa

1 bedroom • 1 bathroom • sleeps 4

from £93 / night

£513 / week

Holiday apartment with shared pool in Le Piazze

Le Piazze apartment

3 bedrooms • 1 bathroom • sleeps 6

6 Reviews

from £71 / night

£494 / week

Holiday apartment letting

Monteguidi apartment

2 bedrooms • 2 bathrooms • sleeps 5

from £118 / night

£698 / week

Holiday villa with swimming pool in Cetona

Cetona villa

10 bedrooms • 9 bathrooms • sleeps 20

21 Reviews

from £611 / night

£4,155 - £6,487 / week

Apartment letting in Colle di Val d'Elsa with shared pool

Colle di Val d'Elsa apartment

3 bedrooms • 2 bathrooms • sleeps 6

from £134 / night

£770 / week

Holiday apartment rental

Sarteano apartment

2 bedrooms • 1 bathroom • sleeps 6

from £134 / night

£934 / week

Pienza holiday home rental

Pienza house

2 bedrooms • 2 bathrooms • sleeps 4

5 Reviews

from £104 / night

£723 / week

Monticiano holiday villa rental

Monticiano villa

2 bedrooms • 2 bathrooms • sleeps 4

from £217 / night

£1,443 / week

Holiday farmhouse in San Gimignano

San Gimignano farmhouse

2 bedrooms • 2 bathrooms • sleeps 6

7 Reviews

from £94 / night

£713 - £1,189 / week

Holiday home letting

Sarteano house

2 bedrooms • 2 bathrooms • sleeps 4

from £206 / night

£1,232 / week

Holiday home in Rigomagno

Rigomagno house

3 bedrooms • 2 bathrooms • sleeps 4

1 Reviews

from £91 / night

£636 / week

Apartment rental in Radda in Chianti with shared pool

Radda in Chianti apartment

1 bedroom • 1 bathroom • sleeps 4

2 Reviews

from £89 / night

£622 / week

Caprera holiday apartment rental

Caprera apartment

1 bedroom • 1 bathroom • sleeps 2

2 Reviews

from £89 / night

£563 / week

Sarteano holiday farmhouse rental

Sarteano farmhouse

4 bedrooms • 2 bathrooms • sleeps 9

from £431 / night

£3,017 / week

Holiday farmhouse in Monteguidi

Monteguidi farmhouse

1 bedroom • 1 bathroom • sleeps 3

from £82 / night

£360 / week

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Top Destination reviews

Tuscany Villa with pool - Villa le Capanne holday in private villas
A magical Christmas

We have just returned from a wonderful Christmas break in this beautiful setting where we also enjoyed blue skies and sunshine every day. Le Capanne is a comfortable and cosy villa set within the most spectacular scenery. We were greeted by our hosts Gina and Franco who had left us a generous welcome pack which was perfect to get us started before we went shopping for our provisions. Gina and Franco were the perfect hosts being available but unobtrusive. Franco visited more than once a day to keep the heating fired up but we hardly knew he was there. Gina produced some delicious homemade delights for us to enjoy. All in all, we would highly recommend a stay at Le Capanne and it provides a good base for visiting other places such as Pisa, Florence and Siena. We would love to return another time.see more
Charming Cottage in Peaceful Country Setting - Sleeps 6
Beautiful setting in Tuscan countryside near Montepulciano

We rented the main living area of this apartment with a loft bedroom upstairs. It's in a lovely setting in the Tuscan countryside surrounded by vineyards and beautiful scenery. It is so peaceful and quiet; a nice respite after a more hectic visit to Florence. Laura was an excellent host making sure we had everything we needed. The apartment was very clean and lovely inside with exposed beams in the ceiling and tastefully decorated. The patio in the back was a relaxing to sit and view the surrounding landscape. If we visit Tuscany again we will be certain to stay here again.see more
**RATED REDUCED FOR SUMMER MONTHS* Exquisite 7 bedroom property - Private Pool
Great for our family gathering

This is a beautiful villa in Tuscany. We had a large family gathering for a week in June and it was the perfect spot for us. Exceptional Villas organised a chef to cook for us some nights and that was a great experience. True Italian food in Tuscany! The surroundings of the villa are stunning and we really got a true taste of Tuscan life. Looking forward to coming back again next year.see more
Monache 4 Farmhouse holiday rental with private pool and garden in San Gimignano
This was a grower!

I wasn’t certain that we had booked the right place when we first arrived. The property is oddly named as a farmhouse but is actually the basement and ground floor of a converted convent with the upper floors of the convent occupied by local Italian families. They however kept their shutters firmly closed all day to keep the heat out and as a consequence you are never even aware of them. The apartment (number four) was very clean and well presented. It was a little light on cooking kit (no serving bowls for example) and one or two of the five beds were not very comfortable. Elisabetta and Massimo could not have been more helpful or friendly if they had tried. They have a little shop near the reception area stocked with emergency essentials and there was also a large supply of great quality free vegetables including potatoes, garlic, Onions and fantastic tomatoes. The nearest shop is a 15 minute drive away in Montaione Coop (poor) or Castelfiotentino Lidl etc (Much better) so the Little honesty shop is a good option if you just need a couple of things. The pool is a nice size, chlorine, about 2/5 To a half is shallow-ish for children. Each apartment has an allotted good quality umbrella and sun loungers and seating. Whilst the view from summer parts of the garden across the valley is very beautiful, there is no actual view from the pool area due to the hedges which are presumably there to stop the wind. That said, I was quite surprised by the largish electric pylons striding down the hill! If you look closely in the photos, you can see the power lines. Oddly, you stop noticing them very quickly! We met lovely family is from Poland and Germany and hope to keep up with them! The children all played together really happily and communicated in English. All in all, we had a very relaxing time and were sad to leave.see more
Villa with private pool, air conditioning, quiet area & nice views 3km from town
Comfortabel and pleasant stay

Nice house on hillside with beautiful view into the valley. All bedrooms are equipped with airconditioning so your sleep is with windows closed ( no mosquitoes and comfortable temperature). We stayed during a very hot period in july but had good night rests. Almost every day in the early afternoon a breeze from the west is cooling down the house. Good wifi coverage , also down at the pool. Supermarket ( middle size COOP ) is downtown at about 10 minute drive. We had fresh tasteful tomatoes and vegetables from the garden and one evening Mr Rafaelle prepare a pizza diner for us , made by his friend and family in the pizza oven behind the garden house. What a wonderful Italian experience was that! We had easy communication through cellphone text messages.see more
Beautiful apartment with pool and great views of San Gimignano
The most wonderful stay in San Gimignano

We had a fabulous week in this stunning property. The owners were very hospitable and were able to book us in at very short notice. The apartment is very clean and well equipped with everything you need. The location is perfect to explore Tuscany, with amazing views of San Gimignano and we were recommended some great local restaurants and wineries. Thank you so much for sharing your apartment and will definitely visit again!see more

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